Month: August 2021

Synthetic Route of 791642-68-7, The chemical industry reduces the impact on the environment during synthesis 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: A microwave vial was charged with 1,4-diiodobenzene or l-bromo-4-iodobenzene (1.0 equiv), Cul (20 mol%), BINOL (20 mol%), and 3P04 (2 equiv.). The vial was capped and then evacuated and backfilled with Ar. Dialklyamine (1.2 equiv) and DMF were then added. The resulting mixture was stirred at rt for 2 to 4 d. The mixture was diluted with EtOAc, filtered through a cake of Celite and the filtrate was concentrated to give the crude product. Crude product was purified by flash chromatography to give the title compound.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-iodo-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; PAULS, Heinz W.; LAUFER, Radoslaw; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; LANG, Yunhui; PATEL, Narendra Kumar B.; EDWARDS, Louise G.; NG, Grace; SAMPSON, Peter Brent; FEHER, Miklos; AWREY, Donald E.; WO2013/53051; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 20555-91-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

(R)-2-(3,4-Dichloro-phenylamino)-propionic acid (62% ee) A mixture of 6.00 g (22.00 mmol) 3,4-dichloroiodobenzene, 2.94 g (33.00 mmol) D-alanine, 0.42 g (2.20 mmol) copper(I) iodide, 0.96 g (4.40 mmol) 2-hydroxybenzaldehyde phenylhydrazone, 14.00 g (66.00 mmol) tri-potassium phosphate in 32 ml of N,N-dimethylformamide was stirred at 80 C. for 16 h under argon, then after cooling diluted with water and acidified to pH 3 by addition of 25% aq. HCl solution. The mixture was extracted with EtOAc (3*), the organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2; dichloromethane/MeOH 95:5 to 4:1) afforded 3.11 g (60%) of the title compound (as 81:19 mixture of the (R) and (S) stereoisomers, BGB-175*0.25 column) as light brown solid. MS: 231.9 (M-H-, 2Cl).

The chemical industry reduces the impact on the environment during synthesis 1,2-Dichloro-4-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; US2011/92698; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103440-52-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 103440-52-4 name is Methyl 2-Iodo-5-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A degasssed mixture of ester EX-25A (10.35 g, 0.037 mol)), Pd(dba)3 (0.017 g, 0.018 mmol)), dppf (0.025 g, 0.045 mmol)) and Zn(CN)2 (2.6 g, 0.02 mol) in DMF (100 mL) was heated to 120 C. for 2 hours. The reaction mixture was poured into water and ethyl acetate. The organic layer was washed with water (2) and brine (1). The organic layer was collected, dried (MgSO4) and the solvent removed in vacuo to give 5.28 g methyl 2-cyano-5-methylbenzoate (EX-25B) as a brownish oil with m/z+1=176.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-Iodo-5-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Pharmacia Corporation; US6664255; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 31599-60-7, Product Details of 31599-60-7

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 755027-18-0, Recommanded Product: 1-Bromo-4-iodo-2-methoxybenzene

To a solution of l-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al., US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 90C for 40 minutes, cooled to RT and poured into 2.4-L 1 M HCl. After stirring for 30 minutes, the solid was filtered, suspended in EtOH (230 mL) heated to reflux and allowed to cool to RT with stirring overnight. The solid was filtered and washed with 1 : 1 EtOH hexane (50 mL) to give the title compound. LRMS ESI+ (M+H)+ 257.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK & CO., INC.; WO2008/57208; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2468-56-6, name is 6-Iodohex-1-yne, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 2468-56-6

To a stirred solution of iodo compound 20 (6.0 g, 28.84 mmol) in anhydrous DMF (30 mL) was added sodium azide (9.37 g, 144.20 mmol) at 0 C under argon atmosphere. The resulting mixture was stirred at rt for 3.5 h, then quenched with ice cold water (50 mL) and extracted with EtOAc (2 * 40 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentratedin vacuo. The crude residue was purified by silica gel column chromatography using 10% EtOAc/hexane to afford azide compound 21 (3.23 g, 91%) as a pale-yellow liquid. HRMS (ESI) m/z calcd for [C6H9N3+H]+: 124.0875, found 124.0218. 1H NMR (400 MHz, CDCl3): delta 3.31 (t, J = 6.7 Hz, 2H), 2.24 (td, J = 6.8, 2.5 Hz, 2H), 1.97 (t, J = 2.6 Hz, 1H), 1.77-1.70 (m, 2H), 1.65-1.58 (m, 2H). 13C NMR (100 MHz, CDCl3): 83.6, 68.9, 50.9, 27.8, 25.5, 18.0.

The synthetic route of 2468-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagendra Reddy, Chintam; Grant, Gail E.; Ye, Qiuji; Powell, William S.; Patel, Pranav; Sivendran, Sashikala; Chourey, Shishir; Wang, Rui; Anumolu, Jaganmohan R.; Rokach, Joshua; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 116 – 125;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 328-73-4, Safety of 1-Iodo-3,5-bis(trifluoromethyl)benzene

Example 3. Preparation of an anion receptor (3); [Reaction Scheme 5]ClCHCCl3l-Iodo-3,5-bis-trifluoromethyl-benzene (3,5-Bis-trifluoromethyl-phenyl)-difluoro-amine 34g of l-iodo-3,5-bis-(trifluoromethyl)benzene (lOOmmol) and 35mL of tetrachloroethane were placed in a 10OmL round flask connected to a glass manifold system having an expansion valve, and the entire system went through 3 freezing – defreezing cycles under vacuum to remove air therein. The system was then filled with 6.7Og of tetrafluorohydrazine (64mmol), and the mixture was heated at 6O0C for 2 hours. During the heating process, the pressure was dropped from the lowest 525mmHg to 368mmHg. When excess gas fraction was analyzed by mass spectroscopy, it was discovered that 5.63g of tetrafluorohydrazine (54mmol) was consumed. Obtained dark colored solution was treated with mercury to remove iodine therein. A substantially transparent solution thusly obtained was then distilled to yield (3,5-bis-trifluoromethyl- phenyl)-difluoro-amine (see the Reaction Scheme 5).1H NMR (300MHz, CDCl3): ppm 7.75 (s, 2H), 8.05 (s, IH); 13C NMR (CDCl3): ppm 112.1, 113.2, 115.2, 119.6; 19F NMR (CDCl3): ppm -53.7, -64.12

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; KYUNGWON ENTERPRISE CO., LTD.; WO2007/126262; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 401-81-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To 1,4-dioxane (200 mL), 1,10-phenanthroline (2.52 g, 13.98 mmol) and copper(I) iodide (2.53 g, 13.28 mmol) were added, and cesium carbonate (36.16 g, 111.0 mmol), diethyl malonate (17.76 g, 111.0 mmol) and 3-iodobenzotrifluoride (25.12 g, 92.35 mmol) were then added thereto. After stirring under reflux for 7.5 hours, the reaction mixture was cooled to room temperature. To the reaction mixture, 1 N hydrochloric acid was added, and the mixture was filtered with a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and the filtrate was distilled off under reduced pressure with an evaporator. The resulting crude product was purified by silica gel chromatography to obtain the title compound (21.26 g, 75.7%). 1H-NMR (CDCl3) delta 7.72-7.57 (3H, m), 7.49 (t, 1H, J=7.8 Hz), 4.66 (1H, s), 4.32-4.15 (4H, m), 1.32-1.22 (6H, m)

The chemical industry reduces the impact on the environment during synthesis 1-Iodo-3-(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Kayaku Kabushiki Kaisha; Hasegawa, Shinji; Kamo, Tomohiro; Kagohara, Yuma; Miyake, Takaaki; Kobayashi, Takeru; Matsuda, Ryusei; Asano, Shu; Kudamatsu, Akio; (43 pag.)US2018/310564; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 54413-93-3, name is 2-Iodo-5-methoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-5-methoxybenzoic acid

General procedure: A dry sealable vial was charged with sulfonimidamide 4a (368 mg, 2.00 mmol), 2-iodobenzoic acid (494 mg, 2.00 mmol), CuI (76 mg, 0.40 mmol), and K2CO3 (690 mg, 5.00 mmol) in anhyd DMF (5.0 mL). After heating to 100 °C for 2 h, the heterogeneous mixture was cooled to r.t. The mixture was diluted with water (10 mL), acidified with 2 M HCl and extracted with EtOAc (3 × 30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by CombiFlash chromatography (silica gel, n-hexane/EtOAc, 6:4) to afford the desired product 7a as a cream solid; yield: 633 mg (90percent).

According to the analysis of related databases, 54413-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sen, Indira; Sasmal, Swarnendu; Hall, Roger G.; Pal, Sitaram; Synthesis; vol. 48; 21; (2016); p. 3743 – 3752;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 481075-58-5, name is 2-Bromo-1-iodo-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H3BrF3I

General procedure: To a stirred solution of o-bromoiodobenzene (1.3 ml, 10 mmol) in THF (10 ml) wasadded dropwise a solution of i-propylmagnesium chloride (2.0 M in THF, 5 ml, 10mmol) at -40 C. After 1 h, PCl3 (0.9 mL, 10 mmol) was added and stirred for 40 minat the same temperature. The mixture was then allowed to stand at room temperaturefor 12 h and cooled at -40 C again. A solution of proper arylmagnesium bromide (1.0M in THF, 22 ml, 22 mmol) was added dropwise. After 1 h, the resulting mixture wasthen stirred at room temperature overnight. Saturated aqueous solution of ammoniumchloride was added and the reaction mixture was extracted with Et2O three times. Thecombined organic layer was washed with water and brine and dried over magnesiumsulfate. The solvent was then evaporated in vacuo and the residue was purified bysilica gel column chromatography with hexane as eluent to afford the correspondingphosphines. After oxidation by H2O2 in acetone, the crude products were purified byusing flash chromatography with ethyl acetate as eluent, giving the pure products.Compounds 1d, 1e, 1f, 1l has been reported in our previous work.

According to the analysis of related databases, 481075-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Yan; Ma, Wei-Yang; Sun, Qiao-Ying; Cui, Yu-Ming; Xu, Li-Wen; Synlett; vol. 28; 12; (2017); p. 1432 – 1436;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com